Triethylamine → HCID 89853740, compound

HRID 931100Notes

Reaction equation

HRID 931100 reaction equation
FC(F)(F)C(O)=O.[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[N:18]3[CH2:19][CH2:20][CH2:21][C:17]3=[CH:16][N:15]=2)[CH2:9]1.C(N(CC)CC)C.Cl[C:30]1[N:35]=[C:34]([NH2:36])[C:33]([N+:37]([O-:39])=[O:38])=[CH:32][CH:31]=1>C(#N)C>[CH:16]1[N:15]=[C:14]([CH:10]2[CH2:11][CH2:12][CH2:13][N:8]([C:30]3[N:35]=[C:34]([NH2:36])[C:33]([N+:37]([O-:39])=[O:38])=[CH:32][CH:31]=3)[CH2:9]2)[N:18]2[CH2:19][CH2:20][CH2:21][C:17]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 89853889HCID 89853889, compound

Product 1

HCID 89853740HCID 89853740, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(piperidin-3-yl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole trifluoroacetate salt (94 mg) in anhydrous acetonitrile (1.1 mL) at 10° C. was added triethylamine (130 μL, 0.93 mmol). Then 6-chloro-3-nitropyridin-2-amine (39 mg, 0.2 mmol) was added. The reaction mixture was shaken at 80° C. for 2 h and then for 18 h at room temperature. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane (3 mL). The mixture was washed with a saturated aqueous solution of sodium bicarbonate (1 mL), washed with water (1 mL), washed with brine (1 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (0-10% methanol in dichloromethane) to afford 6-(3-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-3-yl)piperidin-1-yl)-3-nitropyridin-2-amine as a yellow oil (60 mg, 82%). MS (ES+) (M+H) 329.2; LCMS retention time: 1.61 minutes (Method L).

Workup

  1. waitfor 18 h at room temperature
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane (3 mL)
  4. washThe mixture was washed with a saturated aqueous solution of sodium bicarbonate (1 mL)
  5. washwashed with water (1 mL)
  6. washwashed with brine (1 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified via flash chromatography (0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-b593e8bb707e4cd9919d2aba661431f1
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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